HCID 59855507, compound → HCID 59855503, compound

HRID 2113197Notes

Reaction equation

[CH2:1]([C:5]1[O:6][C:7]2[CH:39]=[CH:38][CH:37]=[CH:36][C:8]=2[C:9]=1[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[C:19]([N+:33]([O-])=O)[CH:18]=2)=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH3:4]>C(O)C.C(O)(=O)C.[Fe]>[CH2:1]([C:5]1[O:6][C:7]2[CH:39]=[CH:38][CH:37]=[CH:36][C:8]=2[C:9]=1[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[C:19]([NH2:33])[CH:18]=2)=[CH:15][CH:16]=1)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 120 °C

Procedure

A solution of 2-butyl-3-[3′-nitro-4′-(3-phenyl-propoxy)-biphenyl-4-ylmethyl]-benzofuran (53 mg, 0.105 mmol) in ethanol (1 mL) and acetic acid (1 mL) was treated with Fe (26.4 mg, 4.5 equiv., 0.472 mmol) and heated to 120° C. for 3 h. After cooling to room temperature, the solution was poured into a 20% aq NaOH/ice water solution (Ph>8) and extracted with ether (3×20 mL). The combined organic layers were washed with water, sat'd aq NaCl, dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification by prep thin layer chromatography (25% ethyl acetate in heptane) afforded 4′-(2-butyl-benzofuran-3-ylmethyl)-4-(3-phenyl-propoxy)-biphenyl-3-ylamine (14.5 mg, 29%).

Workup

temperatureAfter cooling to room temperature
extractionextracted with ether (3×20 mL)
washThe combined organic layers were washed with water
dry with materialdried over anhydrous MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customPurification by prep thin layer chromatography (25% ethyl acetate in heptane)

Sources & evidence

ORD record: ord-d9cc9510830e4979a7f7c9786d65fc2b
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07524878B2

Reaction notes

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